1,3-双(叔丁基二甲基硅氧基)丙烷 | 82112-22-9

• 物质功能分类: 化学试剂 - 有机试剂 - 硅氧烷
• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 中文名称: 1,3-双(叔丁基二甲基硅氧基)丙烷
• 英文名称: 2,2,3,3,9,9,10,10-octamethyl-4,8-dioxa-3,9-disilaundecane
• 英文别名: tert-butyl-[3-[tert-butyl(dimethyl)silyl]oxypropoxy]-dimethylsilane
• CAS: 82112-22-9
• 化学式: C₁₅H₃₆O₂Si₂
• 分子量: 304.621
• InChiKey: NZXKZNIFNMOTHZ-UHFFFAOYSA-N

物化性质

• 熔点：
  115-117 °C
• 沸点：
  295.5±23.0 °C(Predicted)
• 密度：
  0.845±0.06 g/cm3(Predicted)
• 保留指数：
  1489

计算性质

• 辛醇/水分配系数(LogP)：
  5.42
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 储存条件：
  2~8℃，密封保存

反应信息

• 作为反应物：
  描述：

  1,3-双(叔丁基二甲基硅氧基)丙烷 在 tetra-N-butylammonium tribromide 作用下， 以 甲醇 为溶剂， 反应 1.15h， 以99%的产率得到1,3-丙二醇
  参考文献：
  名称：

  Tetrabutylammonium Tribromide (TBATB)−MeOH:  An Efficient Chemoselective Reagent for the Cleavage of tert-Butyldimethylsilyl (TBDMS) Ethers

  摘要：

  [GRAPHICS]TBDMS, THP, and DMT ethers are efficiently deprotected with tetrabutylammonium tribromide in methanol, The apparent order of stability of different protecting group is phenolic TBDMS > 1 degrees OTBDPS > 2 degrees OTBDMS > 2 degrees OTHP > 1 degrees OTHP > 1 degrees OTBDMS > 1 degrees ODMT. TBDMS ether has been cleaved selectively in the presence of isopropylidine, an, Ac, Bz, THP, and TBDPS groups. This method is high yielding, fast, clean, safe, cost effective, and therefore most suitable for practical organic synthesis.

  DOI：

  10.1021/ol006720s
• 作为产物：
  描述：

  1,3-丙二醇 、 N-(特丁基二甲基硅)-N-甲基三氟乙酰胺 在 叔丁基二甲基氯硅烷 作用下， 以 乙腈 为溶剂， 反应 0.08h， 以100%的产率得到1,3-双(叔丁基二甲基硅氧基)丙烷
  参考文献：
  名称：

  N-Methyl-N-(tert-butyldimethylsilyl)trifluoroacetamide and related N-tert-butyldimethylsilyl amides as protective silyl donors

  摘要：

  DOI：

  10.1021/jo00138a032

文献信息

• Silicon-29 NMR Spectra of tert-Butyldimethylsilyl and Trimethylsilyl Derivatives of Some Non-Rigid Diols
  作者：Magdalena Kvíčalová、Vratislav Blechta、Krzysztof Kobylczyk、Ryszard Piekos、Jan Schraml

  DOI：10.1135/cccc19970761

  日期：——

  ²⁹Si NMR spectra of trimethylsilyl (TMS) and tert-butyldimethylsilyl (TBDMS) derivatives of selected diols were measured under standardized conditions (i.e., in diluted CDCl₃ solutions). Application of the recently reported correlation between the chemical shifts in TMS and TBDMS derivatives revealed considerable and systematic deviations which exceeded experimental errors and error estimates from the correlation. Two possible explanations of the deviations are considered: interaction between the two bulky substituent groups and invalidity of the reported correlation for simple hydroxy derivatives. An independent study of analogous derivatives of monohydroxy compounds has shown that the linear correlation holds but the slope and intercept are significantly different from those reported previously on the basis of a study of amino acid derivatives. The data obtained for the diol derivatives fit the new correlation very well and no indication of an interaction between the bulky TBDMS groups was noticed. However, deviations do occur in branched diol derivatives in which branching reduces accessibility of the oxygen atoms surface to associate with proton donors. The largest deviation was found when intramolecular hydrogen bond was formed.

  29Si核磁共振谱测定了选定二醇的三甲基硅基（TMS）和叔丁基二甲基硅基（TBDMS）衍生物在标准化条件下（即在稀释的CDCl3溶液中）。应用最近报道的TMS和TBDMS衍生物化学位移之间的相关性显示出明显和系统性的偏差，超过了实验误差和相关性误差估计。对偏差的两种可能解释是：两个笨重取代基之间的相互作用以及对简单羟基衍生物的报道相关性的无效性。对单羟基化合物的类似衍生物的独立研究表明，线性相关性成立，但斜率和截距与以前基于氨基酸衍生物研究所报告的值显著不同。对二醇衍生物获得的数据非常符合新的相关性，没有发现叔丁基TBDMS基团之间的相互作用的迹象。然而，在支链二醇衍生物中确实存在偏差，其中支链减少了氧原子表面与质子供体结合的可及性。当形成分子内氢键时，发现最大的偏差。
• Functional Analysis of an Aspartate-Based Epoxidation Catalyst with Amide-to-Alkene Peptidomimetic Catalyst Analogues
  作者：Charles E. Jakobsche、Gorka Peris、Scott J. Miller

  DOI：10.1002/anie.200802223

  日期：2008.8.18
• MAWHINNEY, T. P.;MADSON, M. A., J. ORG. CHEM., 1982, 47, N 17, 3336-3339
  作者：MAWHINNEY, T. P.、MADSON, M. A.

  DOI：——

  日期：——
• XIRAO, AKIRA, CHEM. AND CHEM. IND., 1983, 36, N 4, 262-263
  作者：XIRAO, AKIRA

  DOI：——

  日期：——
• Tetrabutylammonium Tribromide (TBATB)−MeOH:  An Efficient Chemoselective Reagent for the Cleavage of <i>tert</i>-Butyldimethylsilyl (TBDMS) Ethers
  作者：Rangam Gopinath、Bhisma K. Patel

  DOI：10.1021/ol006720s

  日期：2000.12.1

  [GRAPHICS]TBDMS, THP, and DMT ethers are efficiently deprotected with tetrabutylammonium tribromide in methanol, The apparent order of stability of different protecting group is phenolic TBDMS > 1 degrees OTBDPS > 2 degrees OTBDMS > 2 degrees OTHP > 1 degrees OTHP > 1 degrees OTBDMS > 1 degrees ODMT. TBDMS ether has been cleaved selectively in the presence of isopropylidine, an, Ac, Bz, THP, and TBDPS groups. This method is high yielding, fast, clean, safe, cost effective, and therefore most suitable for practical organic synthesis.